


Pesterchum Pussy

by Zeath



Category: Homestuck
Genre: Bad Dirty Talk, Boypussy, Dirty Talk, Intersex, M/M, Masturbation, Mutual Masturbation, NSFW, Squirting, Vaginal Fingering, gushing
Language: English
Status: Completed
Published: 2014-12-23
Updated: 2014-12-23
Packaged: 2018-03-03 00:57:52
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,085
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2832362
Author URL: https://archiveofourown.org/users/Zeath/pseuds/Zeath
Summary: <blockquote class="userstuff">
              <p>Dave thought he had to clean out his eyes because obviously he read that wrong. John had a vagina?</p>
            </blockquote>





	Pesterchum Pussy

They had been friends for many years, their long friendship was always full of pranks, video games and sleepovers full of junk food.

But when they started to change due to puberty, something between them had gone askew because they were slipping away from each other. They barely saw each other out of school and even then it was brief and they only seemed to communicate through pesterchum now.

They were talking on that right now, being quite happy actually. They were throwing fake insults back and forth and it was entertaining at the time until Dave had said how John looks like a girl. He hadn’t got a reply back for a while and was worried that he had actually offended his friend, until he heard a pop from pesterchum; John had replied.

**EB: do you really think i look like a girl?**

**TG: that hurt your sensitive feelings egbert?**

**EB: what if i am a girl, what would you do then?**

Was this guy serious? He knows that John’s a dude, they had sleepovers all the time and who would name their daughter John? He was obviously joking. But then Dave started to think; what if John really was a girl? He’s seen enough porn to know what the typical girl is supposed to look like; big tits and a high voice to fit with a vagina. John didn’t look a thing like it. Sure there was a thing about trans people but John didn’t look like the type to be trans, who knows. Dave had never seen what’s between Egbert’s legs so he couldn’t know for sure so he can’t judge.

**TG: i dont know**

**TG: this conversation has gotten very serious all of a sudden**

**EB: what if i told you that i have a vagina?**

Dave thought he had to clean out his eyes because obviously he read that wrong. John had a _vagina_?

What the actual fuck was he going on about? Dave slipped his shades off to rub at his eyes and reread what John had just written over and over. He wanted to say that he would be disgusted or at least feel weird at the subject of his best male friend having a vagina, but the more the thought about it, the more he had images of John slipping fingers in his shorts, pulling them down and sitting on his lap, looking at him with lustful eyes. Sliding his hand down between his legs to rub at his clit and Dave just watching. John suddenly riding his cock. Bouncing until he squirted on his lap.

Holy fuck. Wrong time to get a boner.

**EB: hello?**

**EB: you still there, or has your brain exploded at the sheer thought.**

**TG: no man im here**

**TG: so is that real**

**TG: you having a vagina?**

**EB: well, yeah it’s true, i wouldn’t lie about something like that**

**TG: how do i know you arent just lying to me**

**TG: playing a prank or something**

**EB: well i could give you a picture?**

Dave gulped; he didn’t even realize that he was groping his crotch for a moment, squeezing his cock through his jeans until he tried to type. Fuck, what was he like? Jacking it to his best friend.

**TG: yeah**

**TG: just for proof though**

**TG: no homo**

**EB: is it no homo since i have a vagina?**

**TG: i dunno man**

**[ectoBiologist sent turntechGodhead a picture. Accept?]**

**[Picture accepted]**

Holy fucking shit he had a vagina.

Holy Jesus.

He thought it would be this whole joke and the picture would be John just doing the gun fingers, saying ‘got you’ or something. But no, apparently John did have a fucking vagina because in the picture was his best friend with his legs spread wide, the heels of his socked feet hooked over each arm of the chair and looking away with a blush on his cheeks, showing off his pussy, shaved just like pornstars.

Maybe it was his imagination but it looks like John’s pussy is wet, glistening in the light of the computer screen. His dick just twitched.

**EB: i told you so**

**EB: i haven’t told anyone about that so keep it a secret ok?**

**TG: fuck yeah you told me so**

**TG: and sure ill keep it secret**

**TG: but why dont you have tits then?**

**EB: well, my dad told me about intersex people and apparently i’m one of them**

**EB: funny, huh?**

**TG: yeah funny**

**TG: is it weird if i keep the picture?**

He shouldn’t have written that, fuck that was stupid.

Dave facepalmed himself, over the shades and everything. It was worth a huge slap to the face. He dreaded finding out what John has to say and when the chat popped to alert a new message, Dave didn’t even want to look at what John wrote. Something inside him just peeked through his fingers, perhaps it was hope or stupidity, probably both.

**EB: you can keep it if you give me something in return**

**EB: vice versa and everything right?**

**EB: just in case you use it against me, ill have something to back myself up**

Something in Dave made him think that John had already wanted this to happen. Still, the idea that his friend, who he had been with him through everything and even slept in the same bed together, had what he craved for years.

Hey, it was no surprise to him that he was a virgin; being cool didn’t actually get him the chicks, it just made him look like an asshole. He wanted to see pussy; not the shaved and waxed to perfection pornstar pussy but the real touchable ones.

Sadly, to achieve this it means being nice and not cool but he wouldn’t be able to do that. The picture of John was still up and the more he looked into detail, the more his cock filled with blood and the fact that he had to take a picture made him curse. Falling out his chair to find his webcam, attaching it to the computer and setting it up before tugging down his boxers, revealing his slim cock, veiny and barely showing hair; he’s too proud to trim and being blonde had a plus; no unruly, dark hair just the light curls.

Taking a picture was more of a task than he thought; he wanted it to look like it wasn’t taken by an amateur and when he took a look at his final pieces, nothing looked good enough. Picture after picture, shooting and flashes of the cameras lighting, after almost twenty shots he found the right angle with the right amount of light to not show up the veins so much, plus adding the size to make him look well endowed. Dave was proud of this picture, it was like those adverts for getting a bigger cock and this picture was the ‘after’ shot.

He slipped the file into the pesterchum and waited. A moment later, it was accepted and he couldn’t turn back now, they strayed from the path of best buds and the no homo they put between each other was possibly breached.

Possibly.

**EB: wow dave, that’s something**

**EB: i mean it looks**

**EB: i didn’t think you were going to do it but i’m impressed**

**TG: yeah you dont have to compliment it**

**TG: i know i’m hot**

**EB: so what happens now?**

That was a good question; what should they do?

By now, they had a few choices; pretend this never happened and delete both pictures, split up their long friendship over the fact that John had a pussy or turn this into a good thing where they learn more about each other in a different way. Dave’s cock seemed to like the last choice, still poking out of his crimson boxers and twitching in the cold air.

**TG: this could end up being a good thing egderp**

**TG: you and i**

**TG: we could make something out of this**

**EB: what?**

**TG: well you know**

**TG: youve got a pussy**

**TG: ive got a dick**

**EB: are you saying you want to have sex with me?**

Dave did feel guilty for suddenly making it awkward between them. He moved the picture of John to the side so he could still have a peek at it while typing.

**TG: you dont have to if you dont want to**

**TG: i just thought that it would be easy since we are**

**TG: well you know**

**TG: both virgins**

The feeling of his cock throbbing brought him to the final conclusion that he needed to get off soon. He closed a loose fist around his member and pumped it steadily, feeling how much he ached for something like this to happen.

His cock could feel his need for pussy, his want to be inside something, someone.

He wanted to fuck John.

He shut his eyes as he masturbated slowly, wanting to draw it out as long as he could. He pictured in his head what John would be like in bed; nervous but ready to please, rubbing his clit and stuffing his fingers in his boy cunt.

Fuck.

He was so into the picture of John fucking himself that he almost forgot about the chat until it made a noise.

**EB: i get what you're saying but i dunno**

**EB: what if it effects our friendship?**

**TG: i promise it wont egderp**

**TG: your secret is safe with me and we can experiment with each other as bros**

**TG: bet your dying to know what a cock feels like**

He honestly didn't know where that came from, it was like an urge made him type that out but he did think for a moment about how John would react to actually seeing a cock.

Would he know what to do? Probably not since the whole virgin thing plus the vagina thing.

**EB: dave**

**EB: dont do that**

**TG: oh shit did i offend you?**

**TG: im so sorry dude**

Dave suddenly felt guilt writhe in his stomach; John probably didn't know what a penis was like and he might have had huge identity issues. This could have triggered him enough to actually get him depressed. His cock softens slightly with the little attention he was giving it, glancing at the pesterchum to see what John had said.

**EB: no it just**

**EB: saying stuff like that kinda made me wet**

**TG: oh**

**TG: oh damn**

The blondes eyes widened at the thought of John getting turned on by dirty talk.

He could be rubbing at his folds right now; getting himself lubed up with his own pussy juice before fucking himself with his fingers. The blood flows to his cock once more to pulse heatedly. It couldn't hurt to get his best friend turned on more, he could have some fun with this.

**TG: you get hot and bothered by dirty talk?**

**TG: didnt know you had it in you egderp**

**EB: dave**

**TG: so your pussy likes it when i talk dirty?**

**EG: oh my god dave stop**

**TG: what happens when you get wet?**

**TG: do you rub at it and get yourself all ready for your fingers?**

**TG: or do you have a toy that you use**

**TG: the thought of you using a toy is just wow**

John using a cute little vibrator to fuck his pussy, the wet sounds reverberating through Dave's head. Maybe he had a butt plug and stuffed both his holes up while playing with his clit, fuck it was just so hot to imagine.

Dave hadn't of thought like this about anyone before; John was definitely something special to him but now he wanted more.

**EB: i dont have a toy**

**EB: i just use my fingers**

**TG: shit man**

**TG: my cock is like so hard**

**TG: could cut a diamond with this shit**

He couldn't help himself, reaching down to pull his cock out once more, eyes darting over to where the picture of John with his pussy out, wet and waiting for him to be fucked. He so wanted to pop his best friend's cherry, buy him toys and panties and just fuck him all day. Bury his cock in John and fill him up with his cum.

His cock twitched, leaking precum and getting closer to his release the more that he stroked.

**EB: wow youre hard?**

**EB: im kinda really wet right now**

**TG: i want to see you again dude**

**EB: seriously?**

**TG: is that weird**

**TG: maybe thats really fucking weird but i like it**

**EB: i dont know if its weird but i guess were both getting off so why not?**

**EB: you gotta show me yours too though**

**TG: no prob bro**

**[ectoBiologist send turntechGodhead a picture. Accept?]**

**[Picture accepted]**

**TG: wow**

Dave wasn't expecting anything like this; maybe John spreading his pussy lips once more but holy shit.

His best friend was looking at the camera, same position as the last picture but a slight difference this time; his fingers were fucking his vagina. They were just inside, all two fingers up there like nobody's business.

Dave pointed the camera down to his cock, pumping it with abandon as it took a picture, he then sent it to John who accepted it straight away.

**EB: i want that inside me right now**

**TG: damn if i knew how much of a needy slut you were i would be over there in a second dude**

**EB: what would you do if you were here?**

The blonde could tell his friend was getting more confidence, he was probably fucking his fingers so deep.

 _Fuck_.

He wanted to get laid so bad right now.

**TG: my cock hurts so bad im that hard for you bro**

**EB: dave please**

**TG: ok if i was there i would pin you to your bed**

**TG: rip off your shorts and underwear and just rub your pretty clit**

**EB: fuck dave**

**TG: are you rubbing it right now? imagining it?**

**EB: i am now**

**TG: shit man**

**TG: if i was there i would make you feel so good**

**TG: tell me what you like to do to yourself**

**EB: well i just put two fingers in while rubbing**

**EB: thats enough to make me squirt**

Wait what?

What?

Holy fuck

**TG: you can squirt?**

Holy shit.

He almost came in his fucking pants.

**EB: yeah and im getting so close**

**EB: dave im gonna cum really soon**

**TG: oh man keep going**

**TG: fucking squirt all over yourself**

**EB: fuck shit shit**

And he stop responding.

Dave didn't get a reply back for almost twenty minutes, his cock gonna soft from waiting so long for a reply.

John must have came and passed out or something.

He was on a role for a moment there and it just blew up, Dave wasn't mad about it though; it was their first encounter with sexual intimacy between best friends.

**[ectoBiologist sent a video to turntechGodhead. Accept?]**

What?

**[Video accepted]**

As soon as he clicked the link, a box came up on Dave's screen and he enlarged it, pressing play to have a peek. Of course he knew who would be in the video and sure enough, there was John again with his legs up and over the arms of the chair, having a more desperate face than his past pictures. He pulls off his shirt to show off his perky little nipples, his chest rising and falling as he pants. His voice is hushed when he speaks, being careful of the other people in his house. "Never done this before. I'm kinda nervous."

Dave kept his eyes on his best friend, watching as he reaches down, low and behold, he no longer has underwear either. His fingers run over the lips of his pussy, middle finger dipping between to rub at his clit, other hand suddenly slipping down too and a groan slipped out of his mouth when two of his fingers touched his hole. He was probably sensitive. "Shit."

"Well dang." Dave gulped as his own hand unconsciously grabbed his limp cock and started stroking it back to life. John's head leaned back to rest as he moaned low in his throat, dipping a finger inside himself.

There was a moment where Dave thought he was cum so early; watching his best friend fuck himself on his fingers while making those cute sounds. It was so new to him and his cock didn't know whether to be excited or go limp because hello? This was Dave's best buddy! They did everything together and watching John masturbate was something that shouldn't happen between bros.

"Fuck. Dave."

...

Then again.

John was enticing the blonde, goddamn. He looked so sexy spread out with his eyes closed and body relaxed, pumping two fingers in his pussy while his other hand worked on his clit, his breathing getting faster with each second that passed, moans turning higher in pitch yet still quiet enough for no one to overhear him. "Oh god yes. I'm gonna cum."

Dave sped up his pace on his hand, stroking his cock with the same time that John fucked his cunt, thighs trembling and toes curling in his socks. His crimson eyes trained on his best friend's orgasm face; mouth opening in an 'o' as he groaned loudly, his pussy clenching around his fingers and a spurt of juice coming out to soak his hand and land on the desk. "Oh FUCK. Shit. _Yeaaaah._.."

Dave didn't even realize that he was cumming, jizz leaking out his cock like a fucking fountain before spurting up, catching on his shirt and trousers. At a loss for breath, he glanced up at the screen once more to see John in post orgasmic bliss, smiling goofily and hands laying on his thighs. "I hope you liked that. I guess. Mmm..."

Dave didn't want anything to be awkward about the ordeal, shutting the video off and typing with his clean hand.

TG: that was awesome dude

TG: but i dont want there to be anything weird between us so lets still be bros

**EB: bros that do stuff together**

**TG: yeah if you want**

**EB: i will be expecting you at my house tomorrow**

**EB: my dads gonna be at work so come over**

**TG: sure dude whatever**

Dave was a little more than excited hearing that, so what? Shut up.


End file.
